Man in dapper winter outfitThe inspiration for putting ensembles together can come from anywhere, whether it be an actual item of clothing you own, someone else you have seen, or something else entirely such as a fall landscape.

For this layered winter look, I used a new Goorin Bros hat that I just acquired from their new Philadelphia store. This particular hat is from the heritage country line and features a green / brown felt. I conferred with Charles-Phillipe before the purchase, as he is the resident hat expert here at Bespoke Unit.  As I’ve never owned a hat like this before (typically favoring flat caps), it’s always good to get a second opinion from a friend who knows what they are talking about!

So with new hat in hand, I wanted to create a great cold-weather look around it. The hat provided the earth tone palette, while Philadelphia provided the 20°F (-7°C) weather conditions.

Dapper Street Style – Hat Down

Paul Anthony in custom suit

This is one of my favorite custom suits. It’s a brown / very dark brown herringbone fabric by Holland & Sherry. When designing this suit I wanted it to have an English country feel, thus went with the three roll / two jacket button option, collar wind tab, side vents, ticket pocket, and turn up trousers. That being said, it’s quite a light fabric, making it more than comfortable to wear in an office environment.

As with all of my suits, there is a waistcoat (not pictured / worn) as they offer such versatility not only to add warmth when needed, but also to be used as an “odd”. For example, this fabric looks great under a navy blue suit jacket.

Custom name plate in suit jacket

Holland And Sherry Suit Wind Tab

One cannot neglect accessories and how they can add to / bring your overall color scheme together. This outfit is rooted in earth tones, so I paired a deep purple knit pocket square and a brushed wool green tie, both of which are appropriate cold weather fabric matches, with this brown herringbone suit. Lastly, I wore a pink pinstripe shirt, as white / pink is also a good base layer for most men.

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Putting on herringbone suit jacket

Putting on check wool scarf

Rolex Air-King with pink french cuff

Dr Martens Made in England bootsWhen it gets really cold out, I tend to put the Allen Edmonds away and go with my Dr Martens, as they have a rubber sole. Not only do they cope with adverse weather conditions (e.g. snow & ice) much better due to their chunky tread, but they also keep one’s foot much warmer compared to the leather of a traditional dress shoe. The “Arthur” design shown above is a great boot, as the tone can do well with lots of color schemes. Additionally, it is extremely high quality leather (I really like the unfinished edges), and to top it all off they are Made In England!

Putting on vintage overcoat

The Final Look – Side By Side

Paul Anthony Winter Street Style Goorin Hat

As modern gentlemen, we must accept going from freezing temperatures to overly heated office buildings, shops, restaurants, etc., several times during any given day. Thus, layers become your style and comfort friend. For example, when designing / buying a suit, you should go with traditional style points, but keep in mind where you shall be wearing them most and pick appropriately weighted fabrics.

….oh and don’t forget, top if off with a great hat!

Ensemble Items

  • Hat: Goorin Bros
  • Coat: Ebay Vintage
  • Suit: Holland & Sherry Custom
  • Shirt: Custom
  • Boots: Dr Martens – Arthur (Made In England)
  • Socks: Bass
  • Glasses: Glasses USA
  • Braces: Suspender Superstore
  • Scarf: Banana Republic
  • Gloves: Harris Tweed by Lands End
  • Tie, Lapel Pin, & Pocket Square: Dapper Lapel
  • Tie Bar: Vintage

Please note some of the link in this article are affiliate links. 

About the Author:

Paul Anthony is the founder and creative director at Bespoke Unit. He has had a life long affair with design, watches, fragrance and clothing. Originally from England, he now lives in the USA splitting time between NYC & Philly. Favoring "British Style", but has an overall eclectic taste.

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